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A Historic Escape in the Heart of Boston

Where Revolutionary History Meets Modern Tranquility

Welcome to The Boston Bailey, an exclusive, adults-only retreat designed for the discerning traveler. Nestled in a city defined by its heritage.  Our lodgings offer the perfect blend of old-world elegance and effortless, modern independence.

An Immersive Welcome

From the moment you arrive, you’ll discover that history is woven into the very fabric of our home. Our staircase features a breathtaking two-level mural, a classic masterpiece depicting the iconic Boston Tea Party ship set against the historic glow of Boston Light. This floor-to-ceiling tribute to the harbor serves as a stunning centerpiece, welcoming you to a stay that is as memorable as the city itself.

Your Private Sanctuary

Ascend past the mural to one of our three bright suites; One by Land, Two by Sea and The Paul Revere Suite.  Each space is a curated sanctuary of calm, designed to help you unwind and recharge. To ensure a peaceful and seamless experience, we offer:

  • Adults-Only Ambiance: A quiet, sophisticated atmosphere for total relaxation.

  • Private En-Suite Baths: Your own personal space to refresh and rejuvenate.

  • Modern Independence: Enjoy the freedom of secure, keyless entry and a streamlined self-check-in process.

 

The City at Your Doorstep

Whether you are here for leisure, business, education, or exploration, our location puts the best of Boston within easy reach. Enjoy convenient, stress-free access to:

  • Logan International Airport (perfect for early flights)

  • The Boston Memino Convention & Exhibition Center

  • Prestigious Area Universities

  • Local Beaches & Waterfront Trails

Don’t just visit Boston—immerse yourself in its charm. From our historic maritime art to our peaceful private suites, your unforgettable New England journey begins here.

[View Our Suites & Book Your Stay at www.bostonbaileybnb.com]

WHY CHOOSE THE BOSTON BAILEY

Your Private Boston Sanctuary Awaits!

Discover the perfect blend of historic elegance and modern independence at The Boston Bailey. Designed exclusively for adults, our three curated suites offer a peaceful escape from the city’s hustle without sacrificing its energy. Each room features a private en-suite bath and seamless keyless entry, allowing you to settle in at your own pace with our effortless self-check-in process.

Whether you're here to experience our history, tour world-class universities, attend a conference at the Convention Center, or simply soak in the Atlantic breeze at the nearby beaches, let our home be your sophisticated home base.

Experience Boston Differently – Book Your Suite Today

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COMFORTABLE SUITES & DISTINCTIVE AMENITIES

Stay in one of our bright and comfortable suites, where a delightful ambiance awaits you. Perfect for relaxation, our rooms are designed to help you unwind and enjoy some well-deserved rest after a long day.

AMENITIES

Free Wifi

Air Conditioning

Dishes & Utensils

Luxury bed sheets and towels

Iron & Ironing Board

Printer/Copier

Complimentary Coffee & Tea

Hair Dryer

Sitting Area

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THE TEA PARTY ROOM

The Tea Party Room: Your Morning Sanctuary

Named for the grand maritime mural that anchors our home, the Tea Party Room is the heart of the Boston Bailey experience. Start your morning in our sunlit sitting area, where the aroma of fresh coffee and a selection of fine teas await. Enjoy a light continental breakfast while you map out your day’s adventure or catch up on morning emails in a space designed for quiet inspiration. It’s the perfect, peaceful beginning to your Boston story.

RESERVE YOUR SUITE

Experience the charm of Boston, in all seasons. Book your suite today and treat yourself to a delightful escape in Historic Boston. Enjoy the vibrant culture, Boston Harbor & Beaches, conventions, history, stunning landscapes, and warm hospitality that make this city truly special. Don’t miss your chance for the perfect getaway!

5 stars
"This place was kinda better than a hotel! We had our own bathroom and they had a kitchen stocked with water, coffee, tea, and snacks. I was cold a few nights and reached out to Bill and Maureen, they responded to fast and placed a heater for me to use in the room! so grateful for that because I'm not used to the East Coast cold.....
The location is great, next to a shore that's beautiful and the bus stop to take your straight to downtown Boston is literally a few feet away from their front door."

Julia

California

5 stars
"Bill and Maureen’s place was just as they described it!! Located away from downtown but in a really nice, clean, safe neighborhood. The place was easy to find and check-in process was smooth. There is a Blue Bike station located within a 5min walk, making traveling and exploring the area (including downtown) a breeze. The hosts were very friendly and very responsive. The price was very fair compared to other parts of Boston. The common shared tea room was very convenient with a fridge and coffee/tea. This was my first time in Boston but I would def rent this place again for a future trip"

Laura

North Carolina

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Things To Do In Boston

Explore the vibrant city of Boston, where a wealth of activities awaits you! From thrilling sports events to rich historical sites, there's something for everyone. Come and immerse yourself in the excitement that the city has to offer!

Address

101 P Street

South Boston, MA 02127

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© 2025 The Boston Bailey B&B

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